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1. (WO2004035575) PROCESS FOR THE PREPARATION OF (S,S)-CIS-2-BENZHYDRYL-3-BENZYLAMINOQUINUCLIDINE
Latest bibliographic data on file with the International Bureau   

Pub. No.:    WO/2004/035575    International Application No.:    PCT/US2003/032275
Publication Date: 29.04.2004 International Filing Date: 10.10.2003
Chapter 2 Demand Filed:    11.03.2004    
IPC:
C07D 453/02 (2006.01)
Applicants: PFIZER PRODUCTS, INC. [US/US]; Eastern Point Road, Groton, CT 06340 (US) (For All Designated States Except US).
DSM PHARMACEUTICALS, INC. [US/US]; 5900 N.W. Greenville Boulevard, Greenville, NC 27834 (US) (For All Designated States Except US).
NUGENT, Thomas, C. [US/US]; (US) (For US Only).
SEEMAYER, Robert [DE/US]; (US) (For US Only)
Inventors: NUGENT, Thomas, C.; (US).
SEEMAYER, Robert; (US)
Agent: RICHARDS, John; Ladas & Parry, 26 West 61st Sreet, New York, NY 10023 (US)
Priority Data:
60/419,051 16.10.2002 US
Title (EN) PROCESS FOR THE PREPARATION OF (S,S)-CIS-2-BENZHYDRYL-3-BENZYLAMINOQUINUCLIDINE
(FR) PROCEDE DE PREPARATION DE (S,S)-CIS-2-BENZHYDRYL-3-BENZYLAMINOQUINUCLIDINE
Abstract: front page image
(EN)A process for preparing (S,S)-cis-2-benzhydryl-3-benzylaminoquinuclidine. The process includes the steps of contacting a compound containing a mixture of R- and S-isomers and having Formula (I), with an effective amount of a chiral organic acid in the presence of an organic solvent and an effective amount of an organic carboxylic acid for converting the R-isomer into an acid salt of the S isomer, wherein the organic solvent is capable of solubilizing the compound containing the mixture of R- and S-isomers, while precipitating the acid salt and the organic carboxylic acid is different from the chiral organic acid; neutralizing the acid salt with a base to provide an S-isomer of a chiral ketone of Formula (II), and reacting the chiral ketone with an organic amine in the presence of a Lewis acid to provide the corresponding imine and reducing the imine.
(FR)L'invention porte sur un procédé de préparation de (S,S)-cis-2-benzhydryl-3-benzylaminoquinuclidine. Ce procédé consiste à mettre en contact un composé, contenant un mélange des isomères R et S et de formule (I), avec une quantité efficace d'un acide organique chiral en présence d'un solvant organique et une quantité efficace d'un acide carboxylique organique afin de convertir l'isomère R en un sel acide de l'isomère S. Le solvant organique est capable de solubiliser le composé comprenant le mélange des isomères R et S et de précipiter le sel acide, l'acide carboxylique organique étant différent de l'acide organique chiral; neutraliser le sel acide avec une base pour produire un isomère S d'une cétone chirale de formule (II) et mettre à réagir la cétone chirale avec une amine organique en présence d'un acide Lewis pour produire l'imine correspondant et réduire l'imine.
Designated States: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW.
African Regional Intellectual Property Organization (GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZM, ZW)
Eurasian Patent Organization (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM)
European Patent Office (AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HU, IE, IT, LU, MC, NL, PT, RO, SE, SI, SK, TR)
African Intellectual Property Organization (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, ML, MR, NE, SN, TD, TG).
Publication Language: English (EN)
Filing Language: English (EN)